KR20230083321A - Triazine compounds, materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices, and organic electroluminescent devices - Google Patents

Abstract

An object of the present invention is to provide a triazine compound that contributes to the production of an organic light emitting device having excellent driving voltage and durability. A triazine compound represented by the following formula (1). In formula (1), A and B represent an aryl group having 6 to 20 carbon atoms. L represents a phenyl group or a naphthyl group. n is 0 or 1; C represents any one of the following groups X, Y, and Z. Ar ¹ and Ar ² represent an aromatic hydrocarbon group or a pyridyl group.

Description

Triazine compounds, materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices, and organic electroluminescent devices

The present invention relates to triazine compounds, materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices, and organic electroluminescent devices.

BACKGROUND OF THE INVENTION [0002] Organic electroluminescence devices are used not only for small displays but also for applications such as large televisions and lighting, and their development is being vigorously conducted.

JP 2019-512499 A JP 2018-95562 A WO 2015/111848 A1

Recently, demands from the market for organic electroluminescence devices are increasing, and materials excellent in all of current efficiency characteristics, driving voltage characteristics, and long life characteristics are required.

Here, Patent Document 1 is a triazine compound in which positions 2, 4, and 6 are substituted with other substituents, Patent Document 2 is a triazine compound having a 1,2-phenylene moiety, and Patent Document 3 is a triazine compound having a 2-position Each of the azine compounds substituted with a phenyl group is disclosed.

However, organic electroluminescent devices using the compounds disclosed in Patent Literatures 1 to 3 for electron transport layers do not have sufficient driving voltage and driving lifetime characteristics, and new improvements are required.

One aspect of the present invention is to provide a triazine compound, a material for an organic light emitting device, and an electron transport material for an organic light emitting device, which contribute to the production of an organic light emitting device having a low driving voltage and excellent durability. are doing

Another aspect of the present invention aims to provide an organic light emitting device having a low driving voltage and excellent durability.

According to one aspect of the present invention, a triazine compound represented by formula (1) is provided:

A triazine compound represented by the following formula (1):

In formula (1),

A and B represent an aryl group having 6 to 20 carbon atoms.

L represents a phenyl group or a naphthyl group. n is 0 or 1;

C represents any one of the following groups X, Y, and Z.

Ar ¹ and Ar ² represent an aromatic hydrocarbon group or a pyridyl group.

According to one aspect of the present invention, the triazine compound represented by formula (1) includes triazine compounds represented by the following formulas X(1), formula Y(1) and formula Z(1).

A, B, L, n, Ar ¹ , and Ar ² are each defined as a triazine compound represented by formula X(1), formula Y(1) and formula Z(1).

According to one aspect of the present invention, a triazine compound represented by formula X(1) is provided:

For equation X(1),

A represents any one group selected from the following formulas X(A-1) to X(A-9):

B represents any one group selected from the following formulas X(B-1) to X(B-15):

Ar ¹ is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group;

Ar ² is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group.

According to another aspect of the present invention, a triazine compound represented by the following formula Y (1) is provided:

For equation Y(1),

A represents an aryl group having 6 to 20 carbon atoms;

B is,

An aryl group having 6 to 20 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; or

represents a heteroaryl group having 4 to 30 carbon atoms and having an oxygen or sulfur atom;

Ar ¹ to Ar ² are each independently

An aryl group having 6 to 26 carbon atoms which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group and a phosphine oxide group, or

represents a pyridinyl group which may be substituted with a methyl group or a phenyl group;

n represents an integer from 0 to 1;

L represents any one group selected from the following formulas Y(2-1) to Y(2-5).

According to another aspect of the present invention, a triazine compound represented by the following formula Z (1) is provided:

For equation Z(1),

A represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

B represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

Ar ¹ represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

Ar ² represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group.

According to another aspect of the present invention, a material for an organic light emitting device including the triazine compound is provided.

According to another aspect of the present invention, an electron transport material for an organic light emitting device including the triazine compound is provided.

According to another aspect of the present invention, an organic light emitting device including the triazine compound is provided.

According to one aspect of the present invention, it is possible to provide a triazine compound, a material for an organic light emitting device, and an electron transport material for an organic light emitting device, which contribute to the production of an organic light emitting device having low driving voltage and excellent durability. .

According to another aspect of the present invention, an organic light emitting device having a low driving voltage and excellent durability can be provided.

1 is a schematic cross-sectional view showing an example of a stacked structure of an organic electroluminescent device including a triazine compound according to one aspect of the present invention.
2 is a schematic cross-sectional view showing an example of a stacked structure of an organic electroluminescent device including a triazine compound according to one aspect of the present invention (Device Example-1, etc.).

Hereinafter, a triazine compound according to an aspect of the present invention will be described in detail.

<Triazine compound>

According to one aspect of the present invention, a triazine compound represented by formula (1) is provided:

A triazine compound represented by the following formula (1):

In formula (1),

A and B represent an aryl group having 6 to 20 carbon atoms.

L represents a phenyl group or a naphthyl group.

n is 0 or 1;

C represents any one of the following groups X, Y, and Z.

Ar ¹ and Ar ² represent an aromatic hydrocarbon group or a pyridyl group.

The triazine compound represented by formula (1) is a triazine compound including the case of aspects represented by the following formula X(1), formula Y(1), and formula Z(1).

Hereinafter, aspects represented by expressions X(1), expressions Y(1) and expressions Z(1) will be described.

<Triazine compound X (1)>

A triazine compound according to one aspect of the present invention is represented by the following formula X (1):

For equation X(1),

A represents any one group selected from the following formulas X(A-1) to X(A-9):

B represents any one group selected from the following formulas X(B-1) to X(B-15):

Ar ¹ is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group;

Ar ² is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group.

[For preferred combinations of A, B, Ar ¹ , Ar ² ]

In the triazine compound represented by the formula X(1), the first to eighth aspects that are preferred combinations of A, B, Ar ¹ , and Ar ² are as follows.

· Aspect 1

A represents any one group selected from formulas X(A-1) to X(A-9);

^An aryl group having 6 to 30 carbon atoms, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate,

Ar ² is an aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate

· Second aspect

B represents any one group selected from formulas X(B-1) to X(B-4), (B-7) to X(B-8) and (B-10) to X(B-11) .

· Third aspect

A represents any one group selected from formulas X(A-1) to X(A-9);

^An aryl group having 6 to 30 carbon atoms, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate,

Ar ² is an aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate

· Fourth aspect

A represents any one group selected from formulas X(A-1) to X(A-4);

B represents a group selected from formulas X(B-1) to X(B-4), X(B-7) to X(B-8) and X(B-10) to X(B-11);

^An aryl group having 6 to 30 carbon atoms, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate,

Ar ² is an aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate

· Fifth aspect

A phenyl group, a ¹ -naphthalenyl group, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 2-(1-naphthalenyl)phenyl group, 3-(1-naphthalenyl)phenyl group, 4-( 1-naphthalenyl) phenyl group, 2-(2-naphthalenyl)phenyl group, 3-(2-naphthalenyl)phenyl group, 4-(2-naphthalenyl)phenyl group, 4-phenylnaphthalen-1-yl group, represents a 5-phenylnaphthalen-1-yl group, a 6-phenylnaphthalen-2-yl group, or a 7-phenylnaphthalen-2-yl group;

Ar ² is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phenyl group, a 1-naphthalenyl group, which may be substituted with one or more selected from the group consisting of a diarylboryl group and a phosphine oxide group. , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 2-(1-naphthalenyl)phenyl group, 3-(1-naphthalenyl)phenyl group, 4-( 1-naphthalenyl) phenyl group, 2-(2-naphthalenyl)phenyl group, 3-(2-naphthalenyl)phenyl group, 4-(2-naphthalenyl)phenyl group, 4-phenylnaphthalen-1-yl group, 5-phenylnaphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, and 7-phenylnaphthalen-2-yl group are shown.

· The 6th aspect

A phenyl group, a ¹ -naphthalenyl group, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,

Ar ² is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phenyl group, a 1-naphthalenyl group, which may be substituted with one or more selected from the group consisting of a diarylboryl group and a phosphine oxide group. , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group and 4-biphenylyl group are shown.

· Seventh Aspect

A represents any one group selected from formulas X(A-1) to X(A-4);

B represents any one group selected from formulas X(B-1) to X(B-4);

Ar ¹ represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group;

Ar ² represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group.

· The 8th aspect

A is a group represented by the formula X(A-1);

B is a group represented by the formula X(B-1);

Ar ¹ represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group;

Ar ² represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group.

Hereinafter, the triazine compound represented by formula X(1) may also be referred to as triazine compound X(1).

The definition of the substituent in the triazine compound X (1) and specific preferred examples thereof are respectively as follows.

[About A, B]

For equation X(1),

A represents any one group selected from formulas X(A-1) to X(A-9),

B represents any one group selected from the following formulas X(B-1) to X(B-15):

A represents any one group selected from formulas X(A-1) to X(A-9), and represents any one group selected from formulas X(A-1) to X(A-4) desirable.

B represents any one group selected from formulas X(B-1) to X(B-15), and formulas X(B-1) to X(B-4), X(B-7), X (B-8), preferably represents any one group selected from X(B-10) and X(B-11), and any one selected from formulas X(B-1) to X(B-4) Those representing the group of dogs are particularly preferred.

The combination of A and B is the same as, for example, a combination of a group represented by X(A-1) and a group represented by X(B-1) when the group selected by B does not contain a cyano group. It is preferable to originate.

[For Ar ¹ , Ar ² ]

Ar ¹ is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group;

Ar ² is

An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or

represents a pyridyl group which may be substituted with a methyl group or a phenyl group.

[0059]

Regarding the aryl group having 6 to 30 carbon atoms in Ar ¹ and Ar ² , phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 2-(1-naphthalenyl)phenyl group, 3-(1-naphthalenyl)phenyl group, 4-(1-naphthalenyl)phenyl group, 2-(2-naphthalenyl)phenyl group, 3-(2-naphthyl) Talenyl) phenyl group, 4-(2-naphthalenyl)phenyl group, 4-phenylnaphthalen-1-yl group, 5-phenylnaphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 7-phenylnaphthalen-2- Preferable examples include diyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 9-phenanthrenyl group, 9-anthracenyl group, p-terphenyl group or 2-triphenylenyl group.

These groups may be substituted with an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, but may be substituted with an unsubstituted phenyl group, 1-naphthalenyl group, or 2-naphthalenyl group. , It is more preferably a 2-biphenylyl group, 3-biphenylyl group, or 4-biphenylyl group, and particularly preferably a phenyl group, 2-naphthalenyl group, 2-biphenylyl group or 4-biphenylyl group.

[Specific examples of triazine compound X (1)]

Among the triazine compounds according to one aspect of the present invention represented by formula X(1), specific examples of particularly preferable compounds include X(1-80) from X(1-1) below. The triazine compound according to the aspect is not limited thereto.

<Triazine compound Y (1)>

Triazine compound Y (1) according to one aspect of the present invention is represented by the following formula Y (1):

For equation Y(1),

L represents any one group selected from the following formulas Y(2-1) to Y(2-5):

.

.

Most preferably, any one group selected from formulas Y(A-1) to Y(A-10):

.

.

Most preferably, a group of any one selected from formulas Y(B-1) to Y(B-28):

.

.

[About L]

L represents any one group selected from the following formulas Y(2-1) to Y(2-5):

.

.

[Specific examples of triazine compound Y (1)]

Among the triazine compounds according to one aspect of the present invention represented by formula Y(1), specific examples of particularly preferred compounds include Y(1-179) from Y(1-1) below. Triazine compounds according to aspects are not limited to:

.

.

<Triazine compound Z (1)>

A triazine compound according to one aspect of the present invention is represented by formula Z(1):

For equation Z(1),

A represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

B represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

Ar ¹ represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;

Ar ² represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group.

[About A]

A represents a phenyl group, biphenylyl group, or naphthyl group which may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a cyano group. From the viewpoint of easy synthesis of the triazine compound represented by the formula Z(1) (hereinafter also simply referred to as the triazine compound Z(1)), A is preferably an unsubstituted phenyl group, biphenylyl group or naphthyl group, , It is more preferably an unsubstituted phenyl group or biphenylyl group.

[About B]

B represents a phenyl group, biphenylyl group, or naphthyl group which may be substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a cyano group. From the viewpoint of easy synthesis of the triazine compound Z(1), B is preferably an unsubstituted phenyl group, biphenylyl group or naphthyl group, more preferably an unsubstituted phenyl group or biphenylyl group.

[About Ar ¹ ]

Ar ¹ represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group. In terms of easy synthesis of the triazine compound Z(1), Ar ¹ is preferably an unsubstituted phenyl group or naphthyl group, more preferably an unsubstituted phenyl group.

[About Ar ² ]

Ar ² represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group. In terms of easy synthesis of the triazine compound Z(1), Ar ² is preferably an unsubstituted phenyl group or naphthyl group.

[Specific examples of triazine compound Z (1)]

Among the triazine compounds according to one aspect of the present invention represented by the formula Z(1), specific examples of particularly preferred compounds include compounds represented by the following formulas Z(1-1) to Z(1-95). , The triazine compound according to one aspect of the present invention is not limited to:

.

.

Hereinafter, the use of the triazine compound (1) is demonstrated.

<Materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices>

The triazine compound (1) is not particularly limited, but can be used, for example, as a material for an organic electroluminescent device. In addition, the triazine compound (1) can be used, for example, as an electron transport material for an organic electroluminescence device.

That is, the material for an organic light emitting device according to one aspect of the present invention includes the triazine compound (1). In addition, the electron transport material for an organic electroluminescent device according to one aspect of the present invention includes a triazine compound (1). Materials for organic electroluminescent devices and electron transport materials for organic electroluminescent devices containing the triazine compound (1) contribute to the production of organic electroluminescent devices that are excellent in driving voltage characteristics and current efficiency.

<Organic electroluminescent device>

An organic electroluminescent device according to one aspect of the present invention includes a triazine compound (1).

The configuration of the organic electroluminescence device is not particularly limited, but examples include the following configurations (i) to (vi):

(i): anode / light emitting layer / cathode

(ii): anode / hole transport layer / light emitting layer / cathode

(iii): anode/light emitting layer/electron transport layer/cathode

(iv): anode / hole transport layer / light emitting layer / electron transport layer / cathode

(v): anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(vi): anode/hole injection layer/charge generation layer/hole transport layer/light emitting layer/electron transport layer/cathode.

Hereinafter, an organic light emitting device according to one aspect of the present invention will be described in more detail with reference to FIG. 1 is a schematic cross-sectional view showing an example of a stacked structure of an organic electroluminescent device including a triazine compound according to one aspect of the present invention.

In addition, the organic electroluminescence element shown in FIG. 1 has a so-called bottom emission type element configuration, but the organic electroluminescence element according to one aspect of the present invention has a bottom emission type element configuration. It is not limited to the element configuration. That is, the organic electroluminescence device according to one aspect of the present invention may have a top emission type device configuration or may have other known device configurations.

The organic electroluminescent device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a charge generation layer 4, a hole transport layer 5, a light emitting layer 6, an electron transport layer 7, and The cathode 8 is provided in this order. However, some of these layers may be omitted, and other layers may be added conversely. For example, an electron injection layer may be formed between the electron transport layer 7 and the cathode 8, the charge generation layer 4 is omitted, and the hole transport layer 5 is directly placed on the hole injection layer 3. may be formed.

In addition, instead of the plurality of layers, a single layer combining the functions of a plurality of layers, such as an electron injection/transport layer that combines the functions of an electron injection layer and an electron transport layer in a single layer, is provided. It may be a composition. Further, for example, the single-layer hole transport layer 5 and the single-layer electron transport layer 7 may each consist of a plurality of layers.

[Layer Containing Triazine Compound Represented by Formula (1)]

An organic electroluminescent device contains a triazine compound represented by the formula (1) in at least one layer selected from the group consisting of a light emitting layer and a layer between the light emitting layer and a cathode. Therefore, in the configuration example shown in FIG. 1 , the organic electroluminescent device 100 includes the triazine compound 1 in at least one layer selected from the group consisting of the light emitting layer 6 and the electron transport layer 7 .

In particular, it is preferable that the electron transport layer 7 contains the triazine compound (1). In addition, the triazine compound (1) may be contained in a plurality of layers provided in the organic electroluminescence device, and when an electron injection layer is formed between the electron transport layer and the cathode, the electron injection layer is a triazine compound (1 ) may be included.

In the following, the organic electroluminescent device 100 in which the electron transport layer 7 contains the triazine compound 1 will be described.

[Substrate (1)]

The substrate is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate. Further, in the case of a configuration in which light emission is taken out from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

As a plastic film having light transmission, for example, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, and films made of polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[Anode (2)]

An anode 2 is formed on the substrate 1 (on the hole injection layer 3 side). In the case of an organic electroluminescent element having a configuration in which light is taken out through an anode, the anode is made of a material that transmits or substantially transmits the light.

The transparent material used for the anode is not particularly limited, and examples thereof include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, and aluminum doped oxide. and tin, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide.

Further, in the case of an organic electroluminescent device configured to take out light only from the cathode side, the transmission characteristics of the anode are not important. Therefore, examples of the material used for the anode in this case include gold, iridium, molybdenum, palladium, platinum, and the like.

A buffer layer (electrode interface layer) may be formed on the anode.

[Hole injection layer (3), hole transport layer (5)]

Between the anode 2 and the light emitting layer 6 described later, a hole injection layer 3, a charge generation layer 4 described later, and a hole transport layer 5 are formed in this order from the anode 2 side.

The hole injection layer and the hole transport layer have a function of transferring holes injected from the anode to the light emitting layer, and by interposing the hole injection layer and the hole transport layer between the anode and the light emitting layer, many holes are injected into the light emitting layer at a lower electric field.

In addition, the hole injection layer and the hole transport layer also function as electron barrier layers. That is, electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light emitting layer are transferred to the hole injection layer and/or the electron transport layer by the electron barrier existing at the interface between the light emitting layer and the hole injection layer and/or the hole transport layer. Leakage to the hole transport layer is suppressed. As a result, the electrons are accumulated at the interface in the light emitting layer, resulting in an effect such as an improvement in current efficiency, and an organic electroluminescent device having excellent light emitting performance is obtained.

The material for the hole injection layer and the hole transport layer has at least one of hole injection, hole transport and electron barrier properties. The material of the hole injection layer and the hole transport layer may be either an organic material or an inorganic material.

Specific examples of materials for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted Chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic third A primary amine compound, a styryl amine compound, etc. are mentioned. Among these, a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound are preferable, and an aromatic tertiary amine compound is particularly preferable.

Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'- Bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1- Bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di -p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-di Phenyl-N,N'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether , 4,4'-bis(diphenylamino)quadrylphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di- p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenyl vinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N- Phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4''-tris[N-(3-methylphenyl)- N-phenylamino] triphenylamine (MTDATA) etc. are mentioned.

In addition, inorganic compounds such as p-Si and p-SiC are examples of materials for the hole injection layer and the hole transport layer.

The hole injection layer and the hole transport layer may have a single-layer structure made of one material or two or more materials, or may have a laminated structure made of multiple layers of the same composition or different materials.

[Charge generating layer (4)]

A charge generation layer 4 may be formed between the hole injection layer 3 and the hole transport layer 5 .

The material of the charge generation layer is not particularly limited, and examples thereof include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexane. and carbonitrile (HAT-CN).

The charge generation layer may have a single-layer structure made of one or two or more materials, or may have a laminated structure made of a plurality of layers of the same composition or different compositions.

[Emitting layer (6)]

A light emitting layer 6 is formed between the hole transport layer 5 and the electron transport layer 7 described below. Examples of the material for the light emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs recombine, and light emission occurs as a result.

The light emitting layer may consist of a single low molecular material or a single polymer material, but more generally it consists of a host material doped with a guest compound. Light emission mainly arises from dopants and can have any color.

Examples of the host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi (4,4'-bis (2,2-diphenyl vinyl) -1,1'-biphenyl), BCzVBi (4,4'-bis (9-ethyl-3-carbazovinyl) Ren) 1,1'-biphenyl), TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP(4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-( 9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like.

Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, peripranthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyryl compounds and the like. A fluorescent dopant may be a combination of two or more selected from these.

Examples of the phosphorescent dopant include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

Specific examples of the fluorescent dopant and phosphorescent dopant include Alq3 (tris (8-hydroxyquinoline) aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene , bis[2-(4-n-hexylphenyl)quinoline](acetylacetonato)iridium(III), Ir(PPy)3(tris(2-phenylpyridine)iridium(III)) and FIrPic(bis(3, 5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))), etc. are mentioned.

[0139]

In addition, the light emitting material is not limited to being contained only in the light emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (hole transport layer 5 or electron transport layer 7). In this way, the current efficiency of the organic electroluminescent device can be further improved.

The light emitting layer may have a single-layer structure made of one material or two or more materials, or may have a laminated structure made of multiple layers of the same composition or different compositions.

[Electron transport layer (7)]

An electron transport layer 7 is formed between the light emitting layer 6 and a cathode 8 to be described later.

The electron transport layer has a function of transferring electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a lower electric field.

As described above, the electron transport layer preferably contains a triazine compound represented by the formula (1).

In addition to the triazine compound (1), the electron transport layer may further contain a conventionally known electron transport material. As conventionally known electron transport materials, for example, 8-hydroxyquinolinatolithium (Liq), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis( 8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2 -Methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)-1-naphtolato aluminum, or bis(2-methyl-8-quinolinato)- 2-naphtholatogallium, 2-[3-(9-phenanthrenyl)-5-(3-pyrizinyl)phenyl]-4,6-diphenyl-1,3,5-triazine, and 2-( 4''-di-2-pyridinyl[1,1':3',1''-terphenyl]-5-yl)-4,6-diphenyl-1,3,5-triazine, BCP ( 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8 -quinolinolato)-4-(phenylphenolato)aluminum) and bis(10-hydroxybenzo[h]quinolinato)beryllium);

The electron transport layer may have a single-layer structure composed of one or more types of materials, or may have a laminated structure composed of plural layers of the same composition or different compositions.

When the electron transport layer has a two-layer structure in which the light emitting layer side is the first electron transport layer and the cathode side is the second electron transport layer, the second electron transport layer preferably contains the triazine compound (1).

[Cathode (8)]

A cathode 8 is formed on the electron transport layer 7 .

In the case of an organic electroluminescence element having a configuration in which only light emission passing through the anode is taken out, the cathode can be formed of any conductive material.

As the material of the negative electrode, sodium, sodium-potassium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide (Al ₂ O ₃ ) mixture, indium, lithium/aluminum mixtures, rare earth metals, and the like.

A buffer layer (electrode interface layer) may be formed on the cathode (electron transport layer side).

[Formation method of each layer]

For each layer except for the electrodes (anode, cathode) described above, the material of each layer (if necessary, together with a material such as a binder resin and a solvent), for example, vacuum deposition method, spin coating method, cast method, LB (Langmuir-Blodgett method) can be formed by thinning by known methods, such as a method.

The film thickness of each layer formed in this way is not particularly limited and can be appropriately selected according to circumstances, but is usually in the range of 5 nm to 5 μm.

The anode and cathode can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. At the time of vapor deposition or sputtering, a pattern may be formed through a mask having a desired shape, or after forming a thin film by vapor deposition or sputtering, a pattern of a desired shape may be formed by photolithography.

The film thickness of the anode and the cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

The organic electroluminescent device according to one aspect of the present invention may be used as a type of lamp such as for lighting or as an exposure light source, and may be used as a projection device for projecting an image or a display device for directly viewing still images or moving images (display device). ) may be used as When used as a display device for reproducing moving images, the driving method may be either a simple matrix (passive matrix) method or an active matrix method. In addition, it is possible to manufacture a full-color display device by using two or more organic electroluminescent elements of the present aspect having different luminous colors.

In addition, the triazine compound (1) according to one aspect of the present invention can be synthesized by appropriately combining known reactions (eg, Suzuki-Miyaura cross-coupling reaction).

[Example]

Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not construed as being limited at all by these Examples.

¹ H-NMR measurement was performed using Gemini200 (manufactured by Varian Corporation).

FDMS measurement was performed using M-80B manufactured by Hitachi, Ltd.

The glass transition temperature was measured using DSC7020 (manufactured by Hitachi High-Tech Science Co., Ltd.).

In the DSC measurement, aluminum oxide (Al ₂ O ₃ ) was used as a reference and the sample was measured at 10 mg.

As a pre-measurement treatment, the temperature was raised from 30°C to a temperature equal to or higher than the melting point at a rate of 10°C/min to melt the sample, and then rapidly cooled by bringing the sample into contact with dry ice. Subsequently, the pretreated sample was heated from 30°C at a rate of 10°C/min, and the glass transition temperature was measured.

The emission characteristics of the organic electroluminescent device were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Techno House) by applying a direct current to the fabricated device at room temperature (23° C. 50% RH).

<Triazine compound X (1)>

X Synthesis Example-1 Synthesis of compound X(1-2)

Under a nitrogen stream, 1-chloro-2,5-di(naphthalen-2-yl)benzene (5.0 g, 13.7 mmol), bis(pinacolato)diboron (5.2 g, 20.6 mmol), PdCl ₂ [ (Pcy ₃ )] To a flask containing ₂ (202 mg, 0.27 mmol) and potassium acetate (4.0, 41.1 mmol), 1,4-dioxane (69 ml) was added, and the mixture was stirred at 100°C for 21 hours. After cooling to room temperature, a solid was collected from the reaction solution by suction filtration and washed with 1,4-dioxane. The obtained solid was recrystallized from a methanol (100 ml) solution to obtain 2-[2,5-di(naphthalen-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxabo Rolan's solid (yield: 5.1 g) was obtained.

Under a nitrogen stream, 2-chloro-4,6-di(biphenyl-4-yl)-1,3,5-triazine (4.0 g, 9.5 mmol), 2-[2,5-di(naphthalene- 2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.8 g, 10.5 mmol) and Pd(PPh ₃ ) ₄ (220 mg, 0.19 mmol) was added to the flask containing tetrahydrofuran (191 ml). Further, a 2 M potassium phosphate aqueous solution (14 ml, 28.6 mmol) was added, and the mixture was stirred at 70°C for 22 hours. It was allowed to cool to room temperature, the precipitated solid was collected by suction filtration, and the obtained solid was washed with water and acetone. The obtained solid was dissolved in toluene (2000 ml), activated carbon (1.2 g) was added, and the mixture was heated and stirred at 100°C for 1 hour. Activated carbon was fractionated by suction filtration through a Kiriyama funnel covered with celite, and recrystallized from the filtrate to obtain compound X (1-2) as a white solid (yield: 4.5 g). The glass transition temperature was 116°C.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.85 (m, 1H), 8.26 (m, 5H), 7.90-8.10 (m, 7H), 7.72-7.86 (m, 3H), 7.44-7.65 (m , 16H), 7.39 (m, 3H).

X Synthesis Example-2 Synthesis of compound X(1-4)

Under a nitrogen stream, 2-chloro-4,6-di(biphenyl-4-yl)-1,3,5-triazine (2.3 g, 5.5 mmol), 2-[4-(9-phenanthrenyl) ) [1,1'-biphenyl] -2-yl] -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.0 g, 6.57 mmol) and Pd (PPh ₃ ) To the flask containing ₄ (127 mg, 0.11 mmol), tetrahydrofuran (110 ml) was added. Further, a 2 M potassium phosphate aqueous solution (8 ml, 16.4 mmol) was added, and the mixture was stirred at 70°C for 20 hours. It was left to cool to room temperature, and water and toluene were added and liquid-separated. After distilling off the solvent under reduced pressure, water was added and the precipitated solid was collected by suction filtration, and the obtained solid was washed with water and acetone. The obtained solid was dissolved in toluene (250 ml), activated carbon (0.4 g) was added, and the mixture was heated and stirred at 100°C for 1 hour. Activated carbon was filtered by suction filtration through a Kiriyama funnel covered with Celite, and the solvent was distilled off under reduced pressure. By recrystallizing from a mixed solution of toluene/1-butanol, a white solid of compound X (1-4) (amount 1.5 g) was obtained. The glass transition temperature was 137°C.

¹ H-NMR (CDCl ₃ )δ (ppm): 8.84 (d, 1H), 8.78 (d, 1H), 8.56 (m, 1H), 8.40 (m, 4H), 8.10 (d, 1H), 7.98 ( d, 1H), 7.87 (s, 1H), 7.81 (m, 1H), 7.58-7.73 (m, 13H), 7.31-7.50 (m, 11H).

X Synthesis Example-3 Synthesis of compound X(1-5)

2-[4-(9-phenanthrenyl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2 Except for changing to -[4-(naphthalen-2-yl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The same experimental operation as in Synthesis of X Example-2 was carried out to obtain a white solid of compound X (1-5) (amount 2.5 g).

FDMS:663

X Synthesis Example-4 Synthesis of Compound X (1-75)

2-[4-(9-phenanthrenyl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2 -[4-(naphthalen-2-yl)[1,1':4',1''-terphenyl]-2'-yl]-4,4,5,5-tetramethyl-1,3,2 - Except for changing to dioxaborolane, the same experimental operation as in Synthesis of X Example-2 was carried out to obtain compound X (1-75) as a white solid (amount 1.4 g).

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.69 (d, J = 2.0 Hz, 1H), 8.47-8.41 (m, 5H), 8.03 (d, J = 9.2 Hz, 1H), 7.96-7.88 ( m, 5H), 7.72(dd, J=3.6Hz, 3.6Hz, 2H), 7.69-7.61(m, 8H), 7.58-7.54(m, 2H), 7.52(brd, J=1.6Hz, 1H), 7.50-7.37 (m, 12H).

X Synthesis Example-5 Synthesis of Compound X (1-80)

2-chloro-4,6-di(biphenyl-4-yl)-1,3,5-triazine, 6-chloro-2-[(1,1′-biphenyl)-2-yl]- Compound X (1-80 ) was obtained as a white solid (amount 3.0 g). The glass transition temperature of Compound X (1-80) was 125°C.

^1H -NMR (CDCl ₃ ) δ (ppm): 8.86 (d, J=9.2Hz, 1H), 8.81 (d, J=8.0Hz, 1H), 7.98 (brd, J=6.0Hz, 1H), 7.88 (brd, J=8.0Hz, 1H), 7.84-7.79(m, 2H), 7.79(d, J=1.6Hz, 1H), 7.76-7.66(m, 5H), 7.63-7.57(m, 4H), 7.54-7.32 (m, 14H), 7.13 (dd, J=8.0 Hz, 1.2 Hz, 2H), 6.81 (brt, J=7.2 Hz, 2H), 6.42 (brt, J=7.6 Hz, 1H).

<Triazine compound Y (1)>

Y Synthesis Example-1 Synthesis of compound Y (1-96)

Under a nitrogen stream, 2,4-bis([1,1'-biphenyl]-4-yl)-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxabo rolan-2-yl)phenyl]-1,3,5-triazine (10.0 g, 17.02 mmol), 2,3-dichlorobromobenzene (4.2 g, 18.72 mmol) and Pd (PPh ₃ ) ₄ (393mg, 0.34mmol) was added to the flask containing tetrahydrofuran (170ml). Further, a 2 M potassium phosphate aqueous solution (25.5 ml, 51.06 mmol) was added, and the mixture was stirred at 70°C for 24 hours. It was allowed to cool to room temperature, and the precipitated solid was collected by suction filtration and washed with water and then methanol. The obtained solid was dissolved in toluene and then recrystallized to obtain 2,4-bis([1,1'-biphenyl]-4-yl)-6-(2',3'-dichloro[1,1'- Biphenyl] -4-yl-1,3,5-triazine (amount 9.1 g, yield 88%) was obtained.

Under a nitrogen stream, 2,4-bis([1,1'-biphenyl]-4-yl)-6-(2',3'-dichloro[1,1'-biphenyl]-4-yl- 1,3,5-triazine (9.1 g, 15.05 mmol), phenylboronic acid (12.8 g, 105.4 mmol), palladium acetate (68 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2', To a flask containing 4',6'-triisopropylbiphenyl (X-Phos) (287 mg, 0.60 mmol), tetrahydrofuran (300 ml) was added, and a 2 M potassium phosphate aqueous solution (38 ml, 75.3 ml) was added. mmol) was added, and stirred at 70 ° C. for 90 hours. After cooling to room temperature, the precipitated solid was collected by suction filtration and washed with water and ethanol. The obtained solid was dissolved in toluene (1000 ml) and activated carbon (1.2 g) was added, and the mixture was heated and stirred at 100° C. for 2 hours. The activated carbon was filtered by suction through a Kiriyama funnel covered with celite, and the filtrate was distilled off under reduced pressure. Further, by recrystallization from a toluene (800 ml) solution , to obtain a white solid (amount: 6.9 g, yield: 66%) of compound Y (1-96), with a glass transition temperature of 158°C.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.83 (d, 4H), 8.62 (d, 2H), 7.80 (d, 4H), 7.71 (d, 4H), 7.47-7.57 (m, 7H), 7.42 (m, 2H), 7.32 (d, 2H), 7.17 (m, 3H), 7.08-7.13 (m, 2H), 6.98-7.05 (m, 3H), 6.89-6.94 (m, 2H).

Y Synthesis Example-2 Synthesis of compound Y (1-180)

Under a nitrogen stream, 2-[(1,1'-biphenyl)-4-yl]-4-(naphthalen-2-yl)-6-[3'-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) phenyl] -1,3,5-triazine (15.0 g, 26.7 mmol), {(1,1': 2', 1''-terphenyl )-3′-yl}tripuromethanesulfonate (11.1 g, 29.4 mmol) and Pd(PPh ₃ ) ₄ (927 mg, 0.801 mmol) were added to a flask containing tetrahydrofuran (270 ml). . Further, a 2 M potassium phosphate aqueous solution (40.1 ml, 80.2 mmol) was added, and the mixture was stirred at 70°C for 26 hours. It was allowed to cool to room temperature, the precipitated solid was collected by suction filtration, and the obtained solid was washed with water and acetone. The obtained solid was dissolved in chlorobenzene (800 ml), activated carbon (3.2 g) was added, and the mixture was heated and stirred at 100°C for 1 hour. Activated carbon was filtered by suction filtration through a Kiriyama funnel covered with Celite, and the filtrate was distilled off under reduced pressure. Further recrystallization from a chlorobenzene (700 ml) solution gave compound Y (1-180) as a white solid (amount 13.9 g). The glass transition temperature of compound Y (1-180) was 11°C.

¹ H-NMR (CDCl ₃ ) δ (ppm): 6.95-7.04 (m, 5H), 7.14-7.23 (m, 5H), 7.31-7.33 (m, 1H), 7.38-7.45 (m, 2H), 7.50 -7.65(m, 7H), 7.74(d, J=7.7Hz, 2H), 7.83(d, J=8.5Hz, 2H), 7.94-7.96(m, 1H), 8.03(d, J=8.7Hz, 1H), 8.11-8.13(m, 1H), 8.64-8.67(m, 2H), 8.8(dd, J=8.5Hz, 1.7Hz, 1H), 8.86(d, J=8.7Hz, 2H), 9.32( s, 1H).

<Triazine compound Z (1)>

Z Synthesis Example-1 Synthesis of compound Z(1-2)

2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-diox) under a nitrogen stream Saborolan-2-yl) phenyl] -1,3,5-triazine (3.0 g, 5.1 mmol), {(1,1': 3', 1''-terphenyl) -4'-yl} To a flask containing tripuromethanesulfonate (2.1 g, 5.6 mmol) and Pd(PPh ₃ ) ₄ (133 mg, 0.12 mmol), tetrahydrofuran (51 ml) was added. Further, a 2 M potassium phosphate aqueous solution (7.7 ml, 16.0 mmol) was added, and the mixture was stirred at 70°C for 20 hours. It was allowed to cool to room temperature, the precipitated solid was collected by suction filtration, and the obtained solid was washed with water and acetone. The obtained solid was dissolved in toluene (500 ml), activated carbon (0.5 g) was added, and the mixture was heated and stirred at 100°C for 1 hour. Activated carbon was fractionated by suction filtration through a Kiriyama funnel covered with Celite, and recrystallized from the filtrate to obtain compound Z (1-2) as a white solid (yield: 3.0 g). The glass transition temperature of compound Z (1-2) was 119°C.

¹ H-NMR (CDCl ₃ ) δ (ppm): 8.84-8.79 (m, 4H), 8.71 (t, J=12.0Hz, 1H), 8.64-8.69 (m, 1H), 7.79-7.84 (m, 4H) ), 7.68-7.77 (m, 9H), 7.27-7.67 (m, 15H), 7.18-7.24 (m, 1H).

Z Synthesis Example-2 Synthesis of Compound Z (1-13)

2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -yl)phenyl]-1,3,5-triazine, 2-[(1,1'-biphenyl)-2-yl]-4-[(1,1'-biphenyl)-4-yl Z except for changing to ]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine The same experimental operation as in Synthesis Example-1 was carried out to obtain a white solid of compound Z (1-13) (amount 4.4 g). The glass transition temperature of Compound Z (1-13) was 107°C.

FDMS: 689

Z Synthesis Example-3 Synthesis of Compound Z (1-15)

2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -yl)phenyl]-1,3,5-triazine, 2-[(1,1'-biphenyl)-2-yl]-6-(naphthalen-2-yl)-4-[3'- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] -1,3,5-triazine, but in the same manner as in Synthesis Example-1 of Z An experimental operation was performed to obtain a white solid (yield: 9.7) of compound Z (1-15). The glass transition temperature of Compound Z (1-15) was 112°C.

¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20 (t, J = 7.4 Hz, 1H), 7.28 (t, J = 7.3 Hz, 2H), 7.33-7.53 (m, 10H), 7.56-7.63 ( m, 2H), 7.70-7.77(m, 7H), 7.83(d, J=8.6Hz, 2H), 7.94-7.96(m, 1H), 8.02(d, J=8.7Hz, 1H), 8.11-8.13 (m, 1H), 8.70(dt, J=7.4Hz, 1.7Hz, 1H), 8.75(t, J=1.5Hz, 1H), 8.79(dd, J=8.7Hz, 1.5Hz, 1H), 8.85( d, J = 8.5 Hz, 2H), 9.31 (s, 1H).

Next, device evaluation was conducted using the obtained compound.

<X element Example-1 (see FIG. 2)>

(Preparation of substrate 101 and anode 102)

As a substrate having an anode on its surface, a glass substrate with an ITO transparent electrode in which a 2 mm wide indium-tin oxide (ITO) film (film thickness: 110 nm) was patterned in a stripe shape was prepared. Next, after cleaning this substrate with isopropyl alcohol, surface treatment was performed by ozone ultraviolet cleaning.

(Preparation for vacuum deposition)

On the substrate subjected to the surface treatment after cleaning, vacuum deposition of each layer was performed by a vacuum deposition method, and each layer was laminated.

First, the glass substrate was introduced into a vacuum evaporation tank and the pressure was reduced to 1.0×10 ^-4 Pa. Then, in the following order, each layer was produced according to the film formation conditions.

(Manufacture of hole injection layer 103)

Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H- Forming a 10 nm film of fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane at a rate of 0.15 nm/sec, A hole injection layer 103 was manufactured.

(Manufacture of first hole transport layer 1051)

Sublimation purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H- A film of 85 nm of fluorene-2-amine was formed at a rate of 0.15 nm/sec to prepare a first hole transport layer 1051.

(Manufacture of second hole transport layer 1052)

N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1'-biphenyl-4-yl)amine purified by sublimation was formed into a 5 m film at a rate of 0.15 nm/sec. , the second hole transport layer 1052 was fabricated.

From the foregoing, the hole transport layer 105 having a two-layer laminate structure composed of the first hole transport layer 1051 and the second hole transport layer 1052 was fabricated.

(Manufacture of light emitting layer 106)

3-(10-phenyl-9-anthryl)-dibenzofuran purified by sublimation and 2,7-bis[N,N-di-(4-tert-butylphenyl)]amino-bisbenzofurano-9; A 20 nm film of 9'-spirofluorene was formed at a ratio of 95:5 (mass ratio) to prepare the light emitting layer 106. The film formation rate was 0.18 nm/sec.

(Manufacture of first electron transport layer 1071)

2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1 purified by sublimation; A 6 nm film of 3,5-triazine was formed at a rate of 0.05 nm/sec to prepare a first electron transport layer 1071.

(Production of the second electron transport layer 1072)

Compound X (1-2) and Liq synthesized in X Synthesis Example-1 were formed into a 25 nm film at a ratio of 50:50 (mass ratio) to prepare a second electron transport layer 1072. The film formation rate was 0.15 nm/sec.

From the foregoing, the electron transport layer 107 having a two-layer laminate structure composed of the first electron transport layer 1071 and the second electron transport layer 1072 was fabricated.

(Manufacture of cathode 108)

Finally, a metal mask was placed so as to be orthogonal to the ITO stripes on the substrate, and a cathode 108 was formed. For the cathode, silver/magnesium (mass ratio 1/10) and silver were formed into films of 80 nm and 20 nm, respectively, in this order to form a two-layer structure. The deposition rate of silver/magnesium was 0.5 nm/sec, and the deposition rate of silver was 0.2 nm/sec.

From the above, an organic electroluminescent device 100 having a light emitting area of 4 mm 2 as shown in FIG. 2 was manufactured. In addition, each film thickness was measured with a stylus-type film thickness meter (DEKTAK, manufactured by Bruker).

In addition, this device was sealed in a nitrogen atmosphere glove box with an oxygen and water concentration of 1 ppm or less. Sealing was performed using a glass sealing cap and a film-forming substrate (element) using bisphenol F-type epoxy resin (manufactured by Nagase ChemteX Co., Ltd.).

Direct current was applied to the organic electroluminescent device fabricated as described above, and the luminance characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Techno House). As light-emitting characteristics, current efficiency (cd/A) when a current density of 10 mA/cm 2 was passed, driving voltage (V), and device lifetime (h) during continuous lighting were measured. Device lifetime (h) is measured by measuring the luminance decay time during continuous lighting when the manufactured device is driven with an initial luminance of 1000 cd/m2, and measuring the time required until the luminance (cd/m2) decreases by 5%. did

In Tables 1 to 3, the current efficiency, drive voltage, and device life (h) at continuous lighting are the reference value (100) of the results in X Device Reference Example 1, Y Device Reference Example 1, and Z Device Reference Example 1, respectively. expressed as a relative value. The obtained measurement results are shown in Tables 1 to 3.

<Example of X element-2>

In X Device Example-1, except for using Compound X(1-4) instead of Compound X(1-2), an organic electroluminescent device was manufactured and evaluated in the same manner as in X Device Example-1. The obtained measurement results are shown in Table 1.

<Example of X element-3>

In X Device Example-1, except for using Compound X(1-5) synthesized in X Synthesis Example-3 instead of Compound X(1-2), organic electric field A light emitting device was fabricated and evaluated. The obtained measurement results are shown in Table 1.

<X Device Example-4>

In X Device Example-1, except for using Compound X(1-75) synthesized in X Synthesis Example-4 instead of Compound X(1-2), the same method as in X Device Example-1 was used. A light emitting device was fabricated and evaluated. The obtained measurement results are shown in Table 1.

<Example of X element-5>

In X Device Example-1, except for using Compound X(1-80) synthesized in X Synthesis Example-5 instead of Compound X(1-2), the same method as in X Device Example-1 was applied to the organic field A light emitting device was fabricated and evaluated. The obtained measurement results are shown in Table 1.

<X element reference example-1>

In X Device Example-1, except for using Compound 24 described in Patent Document 1 instead of Compound X (1-2), an organic electroluminescent device was produced and evaluated in the same manner as in X Device Example-1. did The obtained measurement results are shown in Table 1.

<Y element Example-1 (see FIG. 2)>

In X Device Example-1, except for Compound Y(1-96) synthesized in Y Synthesis Example-1 instead of Compound X(1-2), an organic light emitting device was prepared in the same manner as in X Device Example-1. was produced and evaluated. The obtained measurement results are shown in Table 2.

<Y element Example-2 (see FIG. 2)>

In X Device Example-1, except for Compound Y (1-180) synthesized in Y Synthesis Example-2 instead of Compound X (1-2), an organic light emitting device was prepared in the same manner as in X Device Example-1. was produced and evaluated. The obtained measurement results are shown in Table 2.

<Y element reference example-1>

In Y element Example-1, except for using the compound disclosed in Example-9 of Patent Document 2 (Japanese Patent Laid-Open No. 2018-95562) instead of compound Y (1-96), X element Example In the same way as in -1, an organic electroluminescent device was fabricated and evaluated. The obtained measurement results are shown in Table 2.

<Z element Example-1 (see FIG. 2)>

In X Device Example-1, except for Compound Z(1-2) synthesized in Z Synthesis Example-1 instead of Compound X(1-2), an organic light emitting device was prepared in the same manner as in X Device Example-1. was produced and evaluated. The obtained measurement results are shown in Table 3.

<Z element Example-2>

In X Device Example-1, except for using Compound Z(1-13) synthesized in Z Synthesis Example-2 instead of Compound X(1-2), the same method as in X Device Example-1 was performed using an organic electric field. A light emitting device was fabricated and evaluated. The obtained measurement results are shown in Table 3.

<Z element Example-3>

In X Device Example-1, except for using Compound Z (1-15) synthesized in Z Synthesis Example-3 instead of Compound X (1-2), the same method as in X Device Example-1 was used. A light emitting device was fabricated and evaluated. The obtained measurement results are shown in Table 3.

<Z Element Reference Example-1>

In Z element Example-1, except for using the compound shown below (ETL-1) described in Patent Document 1 (International Publication No. 2015/111848) instead of compound Z (1-2), X element An organic electroluminescent device was fabricated and evaluated in the same manner as in Example-1. The obtained measurement results are shown in Table 3.

Since the triazine compound (1) according to one aspect of the present invention has a wide band gap and a high triplet excitation level, it is suitable for use in conventional fluorescent devices as well as phosphorescent devices or organic devices using thermally activated delayed fluorescence (TADF). It can be used suitably for an electroluminescent element.

1, 101: substrate
2, 102: anode
3, 103: hole injection layer
4, 104: charge generation layer
5, 105: hole transport layer
6, 106: light emitting layer
7, 107: electron transport layer
8, 108: cathode
51, 1051: first hole transport layer
52, 1052: second hole transport layer
71, 1071: first electron transport layer
72, 1072: second electron transport layer
100: organic light emitting device

Claims (23)

A triazine compound represented by the following formula (1):

In formula (1),
A and B represent an aryl group having 6 to 20 carbon atoms;
L represents a phenyl group or a naphthyl group. n is 0 or 1;
C represents a group of any of the following X, Y, Z:

;
Ar ¹ and Ar ² represent an aromatic hydrocarbon group or a pyridyl group. A triazine compound represented by the following formula X(1):

In formula X(1),
A represents any one group selected from the following formulas X(A-1) to X(A-9):

;
B represents any one group selected from the following formulas X(B-1) to X(B-15):

;
Ar ¹ is
An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or
represents a pyridyl group which may be substituted with a methyl group or a phenyl group;
Ar ² is
An aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or
represents a pyridyl group which may be substituted with a methyl group or a phenyl group. According to claim 2,
A represents any one group selected from formulas X(A-1) to X(A-9);
^An aryl group having 6 to 30 carbon atoms, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate,
Ar ² is an aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; represents a triazine compound. According to claim 2,
A represents any one group selected from formulas X(A-1) to X(A-4);
B is any one selected from the formulas X (B-1) to X (B-4), X (B-7) to X (B-8) and X (B-10) to X (B-11) A triazine compound representing a group. According to claim 2 or 3,
A represents any one group selected from formulas X(A-1) to X(A-4);
B represents a group selected from formulas X(B-1) to X(B-4), X(B-7) to X(B-8) and X(B-10) to X(B-11);
^An aryl group having 6 to 30 carbon atoms, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; indicate,
Ar ² is an aryl group having 6 to 30 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; represents a triazine compound. According to any one of claims 2 to 5,
A phenyl group, a ¹ -naphthalenyl group, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 2-(1-naphthalenyl)phenyl group, 3-(1-naphthalenyl)phenyl group, 4-( 1-naphthalenyl) phenyl group, 2-(2-naphthalenyl)phenyl group, 3-(2-naphthalenyl)phenyl group, 4-(2-naphthalenyl)phenyl group, 4-phenylnaphthalen-1-yl group, 5-phenylnaphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 7-phenylnaphthalen-2-yl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 9-phenanthrenyl group, 9-anthracenyl group , represents a p-terphenyl group or a 2-triphenylenyl group,
Ar ² is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phenyl group, a 1-naphthalenyl group, which may be substituted with one or more selected from the group consisting of a diarylboryl group and a phosphine oxide group. , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 2-(1-naphthalenyl)phenyl group, 3-(1-naphthalenyl)phenyl group, 4-( 1-naphthalenyl) phenyl group, 2-(2-naphthalenyl)phenyl group, 3-(2-naphthalenyl)phenyl group, 4-(2-naphthalenyl)phenyl group, 4-phenylnaphthalen-1-yl group, 5-phenylnaphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 7-phenylnaphthalen-2-yl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 9-phenanthrenyl group, 9-anthracenyl group , A triazine compound showing a p-terphenyl group or a 2-triphenylenyl group. According to any one of claims 2 to 6,
A phenyl group, a ¹ -naphthalenyl group, wherein Ar 1 may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; , 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,
Ar ² is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phenyl group, a 1-naphthalenyl group, which may be substituted with one or more selected from the group consisting of a diarylboryl group and a phosphine oxide group. , A triazine compound showing a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group. According to any one of claims 2 to 7,
A represents any one group selected from formulas X(A-1) to X(A-4);
B represents any one group selected from formulas X(B-1) to X(B-4);
Ar ¹ represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group;
A triazine compound in which Ar ² represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, or 4-biphenylyl group. According to any one of claims 2 to 8,
A is a group represented by the formula X(A-1);
B is a group represented by the formula X(B-1);
Ar ¹ represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group or 4-biphenylyl group;
A triazine compound in which Ar ² represents a phenyl group, 1-naphthalenyl group, 2-naphthalenyl group, 2-biphenylyl group, 3-biphenylyl group, or 4-biphenylyl group. A triazine compound represented by the following formula Y(1):

In expression Y(1),
A represents an aryl group having 6 to 20 carbon atoms;
B is,
An aryl group having 6 to 20 carbon atoms, which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group; or
represents a heteroaryl group having 4 to 30 carbon atoms and having an oxygen or sulfur atom;
Ar ¹ to Ar ² are each independently,
An aryl group having 6 to 26 carbon atoms which may be substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group and a phosphine oxide group, or
represents a pyridinyl group which may be substituted with a methyl group or a phenyl group;
n represents an integer from 0 to 1;
L represents any one group selected from the following formulas Y(2-1) to Y(2-5):

. According to claim 10,
A is a phenyl group, naphthalenyl group, biphenylyl group, naphthylphenyl group, phenylnaphthyl group, binaphthyl group, phenanthrenyl group, anthracenyl group, terphenyl group or triphenylenyl group,
B is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a phenyl group, a naphthalenyl group, and a biphenyl group, which may be substituted with one or more selected from the group consisting of a diarylboryl group and a phosphine oxide group. Ryl group, naphthylphenyl group, phenylnaphthyl group, binaphthyl group, phenanthrenyl group, anthracenyl group, terphenyl group, triphenylenyl group, dibenzofuranyl group, dibenzothienyl group or, spiro [9H-fluorene-9, A triazine compound, which is a 9'-[9H]xanthene]-yl group. According to claim 10,
A is a group selected from a phenyl group, a biphenylyl group, a naphthylphenyl group, a phenylnaphthyl group, a binaphthyl group, or a terphenyl group;
A triazine compound wherein B is a phenyl group, biphenylyl group, naphthylphenyl group, phenylnaphthyl group or terphenyl group which may be substituted with a cyano group. According to claim 10,
A is any one group selected from formulas Y(A-1) to Y(A-10);
A triazine compound wherein B is any one group selected from formulas Y(B-1) to Y(B-28):

. According to any one of claims 10 to 13,
Ar ¹ to Ar ² are each independently a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, which may be substituted with a cyano group, bi A triazine compound that is a phenylyl group, a naphthylphenyl group, a phenylnaphthyl group, a binaphthyl group, an anthracenylphenyl group or a phenylanthracenylphenyl group. According to any one of claims 10 to 14,
Ar ¹ to Ar ² are, each independently, unsubstituted, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, biphenylyl group, naphthyl group A triazine compound that is a tylphenyl group, a phenylnaphthyl group, a binaphthyl group, an anthracenylphenyl group or a phenylanthracenylphenyl group. A triazine compound represented by the following formula Z (1):

In equation Z(1),
A represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;
B represents a phenyl group, biphenylyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;
Ar ¹ represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group;
Ar ² represents a phenyl group or naphthyl group which may be substituted with one or more substituents selected from the group consisting of a fluorine atom, a methyl group and a cyano group. According to claim 16,
Ar ¹ is an unsubstituted phenyl group or naphthyl group;
A triazine compound in which Ar ² is an unsubstituted phenyl group or naphthyl group. The method of claim 16 or 17,
A is an unsubstituted phenyl group, biphenylyl group or naphthyl group,
A triazine compound in which B is an unsubstituted phenyl group, biphenylyl group or naphthyl group. According to any one of claims 16 to 18,
Ar ¹ is an unsubstituted phenyl group;
Ar ² is an unsubstituted phenyl group or naphthyl group, a triazine compound. According to claim 16,
A triazine compound represented by the formulas Z(1-2), Z(1-3), Z(1-4), Z(1-12), Z(1-13) or Z(1-16):

. A material for an organic electroluminescent device comprising the triazine compound according to any one of claims 1 to 20. An electron transport material for an organic electroluminescent device comprising the triazine compound according to any one of claims 1 to 20. An organic electroluminescent device comprising the triazine compound according to any one of claims 1 to 20.

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